#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:56:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180405 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/74/7207461.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7207461
loop_
_publ_author_name
'Bekö, Sándor L.'
'Schmidt, Martin U.'
'Bond, Andrew D.'
_publ_section_title
;
 An experimental screen for quinoline/fumaric acid salts and co-crystals
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1967
_journal_paper_doi               10.1039/c2ce06439a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         '2(C9 H7 N), C4 H4 O4'
_chemical_formula_sum            'C22 H18 N2 O4'
_chemical_formula_weight         374.38
_chemical_name_common            'Quinoline/fumaric acid (2:1)'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.070(3)
_cell_angle_beta                 89.415(3)
_cell_angle_gamma                87.226(3)
_cell_formula_units_Z            1
_cell_length_a                   3.8288(2)
_cell_length_b                   10.6688(5)
_cell_length_c                   12.0072(6)
_cell_measurement_reflns_used    3288
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      3.27
_cell_volume                     451.17(4)
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_collection       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL v.6.12 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7367
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         3.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                1268
_reflns_number_total             1561
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce06439a.txt
_cod_data_source_block           2
_cod_database_code               7207461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2589(3) 0.65214(9) 0.59738(8) 0.0330(3) Uani 1 1 d .
H1 H 0.155(5) 0.682(2) 0.6597(19) 0.080(6) Uiso 1 1 d .
O2 O 0.3141(3) 0.44988(10) 0.75125(9) 0.0506(3) Uani 1 1 d .
N1 N -0.0101(3) 0.73795(10) 0.75829(9) 0.0253(3) Uani 1 1 d .
C2 C -0.1502(3) 0.64764(13) 0.85473(12) 0.0279(3) Uani 1 1 d .
H2A H -0.1680 0.5577 0.8581 0.033 Uiso 1 1 calc R
C3 C -0.2750(3) 0.67615(13) 0.95301(11) 0.0282(3) Uani 1 1 d .
H3A H -0.3724 0.6070 1.0211 0.034 Uiso 1 1 calc R
C4 C -0.2537(3) 0.80459(14) 0.94875(12) 0.0283(3) Uani 1 1 d .
H4A H -0.3365 0.8261 1.0144 0.034 Uiso 1 1 calc R
C5 C -0.0753(3) 1.04231(13) 0.83450(13) 0.0303(3) Uani 1 1 d .
H5A H -0.1582 1.0696 0.8969 0.036 Uiso 1 1 calc R
C6 C 0.0734(4) 1.13441(14) 0.73490(13) 0.0342(4) Uani 1 1 d .
H6A H 0.0956 1.2253 0.7284 0.041 Uiso 1 1 calc R
C7 C 0.1952(4) 1.09577(13) 0.64097(12) 0.0321(3) Uani 1 1 d .
H7A H 0.2971 1.1611 0.5714 0.039 Uiso 1 1 calc R
C8 C 0.1680(3) 0.96587(13) 0.64919(11) 0.0280(3) Uani 1 1 d .
H8A H 0.2519 0.9408 0.5856 0.034 Uiso 1 1 calc R
C9 C 0.0147(3) 0.86772(12) 0.75235(11) 0.0229(3) Uani 1 1 d .
C10 C -0.1082(3) 0.90664(13) 0.84642(11) 0.0242(3) Uani 1 1 d .
C12 C 0.3491(4) 0.52199(13) 0.64544(12) 0.0281(3) Uani 1 1 d .
C13 C 0.4984(3) 0.46608(13) 0.55882(11) 0.0265(3) Uani 1 1 d .
H13A H 0.5978 0.3756 0.5905 0.032 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C12 O1 H1 110.1(11) .
C2 N1 C9 118.46(11) .
N1 C2 C3 123.85(12) .
N1 C2 H2A 118.1 .
C3 C2 H2A 118.1 .
C4 C3 C2 118.63(12) .
C4 C3 H3A 120.7 .
C2 C3 H3A 120.7 .
C3 C4 C10 120.01(12) .
C3 C4 H4A 120.0 .
C10 C4 H4A 120.0 .
C6 C5 C10 120.77(13) .
C6 C5 H5A 119.6 .
C10 C5 H5A 119.6 .
C5 C6 C7 120.33(13) .
C5 C6 H6A 119.8 .
C7 C6 H6A 119.8 .
C8 C7 C6 120.60(13) .
C8 C7 H7A 119.7 .
C6 C7 H7A 119.7 .
C7 C8 C9 120.16(12) .
C7 C8 H8A 119.9 .
C9 C8 H8A 119.9 .
N1 C9 C10 121.79(11) .
N1 C9 C8 119.01(11) .
C10 C9 C8 119.20(11) .
C5 C10 C9 118.93(12) .
C5 C10 C4 123.81(12) .
C9 C10 C4 117.25(11) .
O2 C12 O1 124.33(12) .
O2 C12 C13 121.18(12) .
O1 C12 C13 114.49(11) .
C13 C13 C12 124.04(15) 2_666
C13 C13 H13A 118.0 2_666
C12 C13 H13A 118.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.3090(16) .
O1 H1 0.99(2) .
O2 C12 1.2120(16) .
N1 C2 1.3134(16) .
N1 C9 1.3662(16) .
C2 C3 1.4027(18) .
C2 H2A 0.9500 .
C3 C4 1.3576(19) .
C3 H3A 0.9500 .
C4 C10 1.4170(18) .
C4 H4A 0.9500 .
C5 C6 1.3581(19) .
C5 C10 1.4097(18) .
C5 H5A 0.9500 .
C6 C7 1.411(2) .
C6 H6A 0.9500 .
C7 C8 1.3595(18) .
C7 H7A 0.9500 .
C8 C9 1.4175(18) .
C8 H8A 0.9500 .
C9 C10 1.4162(18) .
C12 C13 1.4841(18) .
C13 C13 1.313(2) 2_666
C13 H13A 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.99(2) 1.63(2) 2.6227(13) 177.1(18)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C9 N1 C2 C3 -0.38(19) .
N1 C2 C3 C4 0.6(2) .
C2 C3 C4 C10 0.09(19) .
C10 C5 C6 C7 0.5(2) .
C5 C6 C7 C8 -0.5(2) .
C6 C7 C8 C9 0.3(2) .
C2 N1 C9 C10 -0.46(18) .
C2 N1 C9 C8 179.49(11) .
C7 C8 C9 N1 179.88(11) .
C7 C8 C9 C10 -0.17(19) .
C6 C5 C10 C9 -0.37(19) .
C6 C5 C10 C4 178.65(12) .
N1 C9 C10 C5 -179.87(11) .
C8 C9 C10 C5 0.18(18) .
N1 C9 C10 C4 1.05(18) .
C8 C9 C10 C4 -178.90(11) .
C3 C4 C10 C5 -179.87(12) .
C3 C4 C10 C9 -0.84(18) .
O2 C12 C13 C13 170.82(17) 2_666
O1 C12 C13 C13 -8.5(2) 2_666
